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đź’š The two hardest people to fire
#29. and why sometimes it’s the only way to go

Hello and Happy Thursday!
There are a lot of things contending for the title of "hardest part of being a People Ops leader," but the one that will always top the list for me is letting people go.
I’ve had several conversations about this recently, and while laying down the hammer on someone’s livelihood never feels good, there are two types of teammates who are especially hard to terminate.
First up is the Brilliant Asshole: a workplace bully and culture killer who teammates absolutely dread collaborating with. Everyone is reluctant to keep them around - except for the fact that they crush it at their job, earning them powerful allies and a whole bunch of undue good will.
Second - and more heartbreakingly - is the Underperforming Sweetheart. This is the person who genuinely cares for their teammates, has the best intentions, and serves as something of a culture totem. (I believe Gen Z has affectionately named this person the “personality hire”) The only problem is their chronic underperformance, dragging on their team’s overall success.
One is politically fraught. The other, a heartbreaker. But both are necessary to nip in the bud, no matter how painful. And today, I want to talk about why.
Yours in ripping off the bandaid,
Jill
P.S. - It’s Pride month! I’m sending love all month long to my brilliant, beloved fellow queers. Out n’ proud, questioning, finding your community, learning our history, stepping more fully into who you are - wherever you are, as whoever you are, I’m celebrating you and wishing you support, reflection, safety, pride, and so, so much joy.
❤️🧡💛💚💙💜
REFLECT ON THIS...
➙ Have you ever worked a job knowing it wasn’t the right fit? How did that feel?
âž™ Have you ever worked with a chronic under-performer or a genius who was a total jerk? How did it impact your own employee experience?
The case for farewell
First, it feels fair to say upfront that making arguments in favor of firing someone feels gross. Even if someone has to go for valid reasons, it’s impossible to separate the decision from the weight of its financial, emotional, and personal impact on the departing employee.
With that, it’s important to look at the bigger picture of what draws us to working in People, being great managers, or influencing our workplace cultures. We believe better is possible, and that everyone deserves a work experience that’s energizing, meaningful, and positive. As sucky as a termination is, sometimes it’s the most powerful decision you can make to protect that experience for your team.
Frankly, keeping a high performing asshole or a lovely poor performer on your team carries a lot of risk - for you as a manager or decision maker, for your team, and for the employee themself. So let’s break down the case for getting these folks off your team, and putting them one step closer to a much more beneficial fit.
Risks of keeping a Brilliant Asshole™ on your team:
For you, the manager or leader
First, let’s state the obvious: managing someone you dread interacting with is exhausting. Showing up to work drained is no way to live, let alone to positively lead others. Beyond that, when you support a high performing jerk’s tenure on your team, you risk signaling that you value output at any cost. In addition to catalyzing a whole bunch of negative outcomes (like poor team morale, burnout, and attrition), an “at all costs” performance culture can prove a ripe environment for shady behavior. Whether for toxic competitiveness, stalemated collaboration, or corner-cutting in the name of a cushier bottom line, even your most stalwart employees wouldn’t be blamed for pulling out all the stops to land in your good graces.
For the employee themself
There’s an important call out here, which is that your tricky teammate’s culture-killing behavior on your team is exactly what would make them a perfect fit at the right place for them. There’s a lid for every pot, and an ideal work culture for every employee - it just isn’t on your team, and the longer they stay, the longer they’re missing out on the opportunity to find a place they can contribute just as they are.
For your team
It may be that the people most harmed by keeping this employee on board are the others on your team or at your organization. Whether intentionally or not, keeping this employee around subjects other teammates to bullying. Moreover, by making excuses for outsized performance, you implicitly devalue others’ performance. It’s almost like implying the suggestion “well if you were a top performer, you could act like a jerk too!” This messy messaging isn’t just painful and confusing, it’s demotivating as all get out. Don’t be surprised if your team’s overall morale drops - quickly - with each act of inappropriate behavior by your high performer that goes unchecked.
Risks of keeping an Underperforming Sweetheart on your team:
For you, the manager or leader
It’s okay to be mindful of your own experience here. Depending on the performance culture at your organization, you may risk putting you and your team under a microscope for “excusing” underperformance. Moreover, if the underperformance is egregious enough, your other teammates are likely taking on additional workload, stress, and responsibility to compensate. Factor in what can be seen as favorable treatment towards a teammate who’s creating undue hardship on their teammates, and your other reports may be harboring resentment towards you, and suffering low engagement.
For the employee themself
For whatever reason - skill, will, mis-match of style, or something else - your performance coaching attempts haven’t landed with this teammate. Intended or not, keeping them under your leadership is hindering them from finding the growth and coaching they specifically need to experience career success. Alternatively, if this role itself isn’t a long term fit for the employee’s skillset and potential, staying in it longer is only going to delay the opportunity to re-evaluate.
For your team
No matter how much teammates may appreciate this person’s cultural and social contributions, continuously “picking up someone else’s slack” can take a toll, particularly if teammates are already approaching burnout. Moreover, other teammates could see this person’s continued tenure as managerial favoritism, inspiring the question of “why is it okay for them to consistently underperform, but not me?"
Now you might be wondering "Jill, what do I do about the brilliant assholes and underperforming sweethearts on my team??” If this is really someone who’s got to go, it may be the case that you already know what you have to do, and I'm sorry to say that it's gonna be really dang hard. But whether you’re preparing for someone’s exit, or hoping to implement some coaching to correct problematic behaviors, I’ve got plenty of resources laid out for you below!
Final thoughts…
I promise I have some good news too, which is that with the right resources for coaching and performance management, much of this conflict can be avoided - or at least managed with respect, empathy, and more open communication. If you fear you’re headed towards your own Brilliant Asshole or Underperforming Sweetheart situation, keep on reading…
YOUR TURN
No, I’m not about to tell you to pick someone on your team and advocate for their termination. But this week’s topic does pose a great opportunity to audit the impact of individuals across your team. Take some time in the coming days to quickly assess your team.
Have you noticed behavior from top performer(s) you wouldn’t support from other teammates?
Is there anyone on your team for whom you make performance concessions based on an otherwise pleasant personality and presence?
Do you have any concern that someone on your team could fit one of these two personas?
There’s hope! If this person hasn’t yet received coaching on underperformance or not-very-cool team behavior, we highly recommend starting with coaching. Dig into the resources we’ve laid out below, and start jumping confidently into the hard work of managing a bit of workplace trickiness.
MORE HELPFUL RESOURCES
Coaching: Even if the concern ultimately results in a termination, quality coaching offers an employee the chance to adapt, and ensures there are no surprises. The resources below offer excellent guidance to coach for poor performance or address tricky behaviors.
This BetterUp article offers a thorough overview for managing under-performance. Starting with a curious, empathetic understanding of the concern, and guiding you all the way through to preparing for a tough decision if necessary, it’s a great jump-off for approaching performance coaching.
It can be tough to find good resources about managing high performing jerks that don’t get too tongue-in-cheek, but this one from Let’s Grow Leaders offers an empathetic, caring approach to improving potentially toxic behavior.
If you’re nervous delivering any level of difficult feedback, this roundup from Jerome Knyszewski on Medium gives a fairly thorough intro to several strategies you use to approach the conversation.
PIP with empathy: Whether or not to institute a Performance Improvement Plan (commonly called a “PIP”) could be the focus of an entire newsletter. That said, if you’re in an organization that relies on PIPs for performance and departure exits, here are some great articles to dig into.
If you don’t know where to start wrapping your mind around Performance Improvement Plans, this primer from Forbes offers good top line context (pros and cons included). I particularly appreciate that they contend a bit with some of the PIP’s historically bad PR.
This First Round article packs in a lot about approaching terminations with accountability, but I’m including it specifically for the “Pre-PIP” and “PIP for Real” guidance; the real meat starts with the section title “Tackle Performance Head On.”
Looking for another approach? Check out the story of “Tim,” an employee struggling with performance, and the approach he and the company came to collaboratively to manage his exit.
Softening the blow: If things do come to a termination, the resources below will help you steady the impact of the departure with the rest of your team.
Terminating a teammate can leave remaining teammates reeling. These 6 tips bring you back to basics on building trust and maintaining energy on your team after a departure.
When it comes to delivering news of a departure to teammates, there’s a delicate balance to strike between what’s appropriate to communicate and what’s necessary to steady the team. This article offers some helpful guidance on appropriate discretion, respect, and context to strike when sharing the news with teammates.
MIDWESTERNERS, ASSEMBLE!
I so love a good reflection session, and mid-year is the perfect time to pause and look back before continuing to charge forth. That’s why I’m so excited to co-host the RfH (that’s “Resources for Humans”) Midwest Virtual meetup on Wednesday, June 12th! Fellow Midwesterners, sign up here. Let’s talk wins, opportunities, and getting laser focused for the second half of the year.
